Alvin and the Teenmunks
by S.M. Jackson
Summary: REWRITTEN. At 15 years old, the Chipmunks and Chipettes are finally in their freshmen year of high school. It seemed like paradise, until they discover two of them have been keeping a secret from the others, which not only ends their friendship, but drives a wedge between siblings, until the others discover something that's been hiding for years. Rated T.
1. Chapter 1

_**The following is a rewrite of my Teenmunks story from some time ago. The story and the designs I've chosen for the Teenmunks are both inspired by the awesome artwork called 'Alvin and the Teenmunks' but ctw36! Also, just for fun, I have composed a little fictional cast for this fic, mostly to feed my own sick desire of this becoming a real Chipmunks thing in the future, which it probably never will.**_

**Alvin and the Teenmunks**

Starring…

**Ross Bagdasarian Jr. as Dave Seville, young Alvin Seville, and young Simon Seville  
Janice Karman as young Theodore Seville, young Brittany Miller, young Jeanette Miller, and young Eleanor Miller  
Jason Marsden as Teenage Alvin Seville  
Rob Paulson as Teenage Simon Seville  
Grey DeLisle as Teenage Brittany Miller  
Tara Strong as Teenage Theodore Seville and Teenage Jeanette Miller  
Kath Soucie as Teenage Eleanor Miller**

At Clyde Crushcup Elementary, the school bell rang to dismiss the students for the day. Walking out of the school, amongst all of the children, were six familiar chipmunk children. There was the cap wearing leader, Alvin, and his brothers, Simon and Theodore. Next to them were their counterparts, Brittany, Jeanette, and Eleanor, the Chipettes. Alvin sighed, "You know what? I was thinking about something today."

Simon jokingly answered, "If it's about you failing the math test, maybe it's because you played video games all week instead of studying."

"That's not at all what I was thinking!"

Simon sighed, "Fine, Alvin. What is it?"

Alvin asked, "What do you think it'll be like?"

Brittany asked, "What are you talking about, Alvin?"

Alvin said, "When we're teenagers!"

"Huh?" All of them asked in unison.

Simon asked, "Alvin, where is this coming from?"

"I don't know. I just thought about it and… just think about everything we'll get to do when we're teens we can't do now! For one, we'll be taller! We'll get to stay up a few hours later."

Brittany said, "Finally go on a _real _date with someone."

Theodore said, "We'd get to watch PG-13 movies without an adult."

Eleanor said, "We'd have our own cell phones."

Simon unenthusiastically added, "Not to mention we'd deal with the downsides of growing up."

Jeanette asked, "Downsides?"

Simon explained, "You know, growing pains, pimples, peer pressure… unlike the peer pressure we already receive… and puberty. Our voices would change… but only slightly, since we're chipmunks… we'll start getting hair in the weirdest places, not to mention you girls would…" Simon paused momentarily and said, "Develop."

Jeanette gulped and blushed, "Develop?"

Eleanor asked, "What's 'develop' mean?" Brittany whispered it into Eleanor's ear, and when she finished, Eleanor said in a somewhat shocked tone, "Oh."

Alvin scoffed, "Who cares?! You gotta take the good with the bad! Yep! I tell you, when we become teens, everything will change for the better! I can feel it!"

**5 years later…**

At the Seville house, the chipmunks were asleep in their beds as an alarm clock went off next to Alvin's bed. As the alarm rang, Alvin groaned and turned it off. 10 minutes later, Dave called from downstairs, "Fellas! It's time to get up! You don't want to miss your first day of High School!" No response. Dave called once more, "Boys, get up! You're going to be late." The chipmunks squirmed in bed as they heard Dave's voice. Everything was calm, until, "Simon, Theodore, ALVIN! Wake up!"

"Okay!" Alvin said, in a slightly deeper voice than what one would normally hear from him. Not only did Alvin's voice change, but so did his brothers' voices. While they still maintained their chipmunk voices, one could tell they sounded older than they once did.

Alvin, Simon, and Theodore got out of bed. At first glance, one could tell they weren't the little chipmunks they use to be. Alvin, Simon, and Theodore were now 14. Simon was still the tallest, at 4 foot 5, Alvin was at 4 foot 2, and Theodore was only at 3'9. Not that much taller than they were as kids, but still, it was something. Not to mention, Simon and Alvin actually grew hair that looked like it belonged on a person. Granted, it wasn't as much hair as the Chipettes had, but it was still visible. As the three teenaged chipmunks got dressed, one could spot the changes in their wardrobe. Alvin still wore his cap and a short sleeved shirt with the giant 'A' on it, and his also wore blue jeans with his outfit. Simon wore a button up blue shirt that had the sleeves rolled to his elbows and black jeans. Theodore wore a stripped green sweater vest over a white button up shirt and a pair of khaki pants. They each still had the shoes the use to wear, since their feet never grew. As the boys left the room, Alvin grabbed a red skateboard, ran a few steps, and hopped right on it! Alvin did a grind down the staircase rail, and crashed right into Dave, who was at the bottom of the stairs with his back turned!

Alvin was on top of a very furious Dave, "Alvin!"

Alvin chuckled nervously, got off of Dave, grabbed his board and bolted out the door, "Later, Dave!"

Simon and Theodore also rushed out the door, following their hell on wheels brother. Once Alvin slowed down and his brothers caught up, Simon glared at him and asked, "You do know when we get home today, you'll be in big trouble, right?"

Alvin asked, "Is that a trick question?"

Simon answered, "It's a no-brainer, Alvin."

Simon was cut off by a deep growling sound. Alvin and Simon turned to Theodore, who was holding his stomach as it growled, "Sorry, guys."

Simon patted his younger brother on the back, "It's okay, Theodore. If it weren't for Alvin's tomfoolery, we could've eaten this morning."

Alvin rolled his eyes, "Oh, sure. It's always Alvin, isn't it?"

Simon answered, "Because it _is _always you, Alvin."

As they turned the corner of the sidewalk, Alvin retorted with, "Can I help it if I'm a free spirit?"

"Yes, you can," Simon answered as deadpan as usual, "What you lack is the ability to do so."

Before Alvin could respond to that, something caught his eye. In front of Alvin and his brothers was Ruby Spears High School, the very place where he and his brothers would spend the next four years of their life. It was three stories high, with a 7 foot high stone staircase that went up to the entrance. There was a part of the school where a giant clock was built into it, showing the time of 7:48, 27 minutes until class. On the side, there was a parking lot for students who have already gotten their licenses and cars. Behind the school were the football field, a baseball diamond, and a soccer field, where many sports events have taken place over the years. At the front of the school was a gold statue of an Eagle, the school mascot. As Alvin marveled at the school, he said, "My brothers… we've made it."

Inside the school, the small group of siblings traveled down the locker filled hallways and took in the sights. From the bulletin boards filled with flyers for various clubs and tryouts for sports teams, to the many trophy cases that adorned the walls, to the staircase that led to 2nd floor of the school.

As Alvin and his brothers wandered the hallways, Alvin said, "You know, I pictured this place more… party-like."

"Well, Alvin, it _is _a school," Simon reminded his red-clad older brother, "Not a Frat house."

Theodore looked around and said, "I don't know. I kind of like it."

Alvin told his baby brother, "Give it time."

Theodore stopped dead in his tracks and asked, "Huh? What do you mean?" As his brothers kept walking, Theodore gave chase, "Hey, wait! What do you mean 'give it time'?"

As the Chipmunks walked the halls, they came to a row of lockers. 3 of them read 68, 69, and 70.

Alvin said, "Well. Here they are."

"These lockers are perfect!" Simon pointed out what was near their lockers, "They're right across from Homeroom, they're next to a water fountain, the vending machines…"

Alvin pointed out, "And it's only a few steps to the boy's room!"

As Alvin pointed this out, a very large guy walked out and said, "Phew! No one go in there for 30 minutes!"

The Chipmunks were quiet for a few seconds, until Alvin said, "Well, 3 out of 4 isn't bad."

As Alvin picked up his skateboard to put into his locker, he and his brothers heard a high voice call from behind, "Morning!" The chipmunks turned to see their now teenaged counterparts, the Chipettes.

Just like Alvin and his brothers, Brittany Jeanette, and Eleanor were 14. However, Jeanette was only at 4'4, Brittany at 4'1, and Eleanor at 3'8. Their hair styles remained the same, but Brittany's ponytail was longer and was fastened by a blue scrunchie. Brittany wore a pink off-shoulder top, a pair of skinny blue jeans fastened by a belt with a oval yellow buckle, red ballet shoes, and a pair of yellow orb earrings. Jeanette wore a stripped blue sweater, a purple skirt, and blue Mary Janes. Eleanor wore a spring green polo shirt, green pants, and brown slip-ons. Of course, one thing that truly stood out to the boys was the Chipettes' now teenaged chests. Not that they were perverts for noticing, but just average teenage boys; or in this case, teenage chipmunks. Course, Eleanor hadn't exactly gotten hers, but her baby fat did give her a simple B-cup, just like her sister, Brittany. However, the biggest out of the three would be Jeanette, who clocked in at a nicely sized C-cup. Though, she didn't take pride in the fact her breasts were big, as apparent with the large textbook she was clutching to her chest in an attempt to hide them. After all, she is Jeanette.

Alvin grinned, "Hello, ladies." Alvin walked over to Brittany, "Well, hello, Brittany. I didn't realize the zoo released you."

Brittany sarcastically laughed, "That's as funny as it was back in elementary school, Alvin."

Alvin asked, "What do you mean by that?"

"Oh, _please_, Alvin," Brittany responded, "You're the only one of us who hasn't gotten out of childhood yet! I mean, seriously! We're in High School, so act like it!"

Alvin laughed at Brittany's words, "Like you're one to talk."

Brittany crossed her arms, "Excuse me?!"

"Come on, Brit. No offense, but you're not exactly Little Miss Mature."

"Yes, I am!"

"No, you're not!"

"I am!"

"Nuh-uh!"

"Yeah-huh!"

"Nuh-uh!"

"Yeah-huh!"

"Nuh-uh!"

"Yeah-huh!"

As Brittany and Alvin went back and forth, Simon whispered to Jeanette, "15 years old and they _still _act like children."

Jeanette said, "Yeah. It's kind of sad," Jeanette then muttered to herself, "In more ways than one."

Simon asked, "Did you say something, Jeanette?"

Jeanette gasped and blushed, "What?! No! I-I-I didn't say anything."

As Brittany and Alvin kept fighting and Simon and Jeanette just watched, Eleanor approached Theodore and said, "Morning, Theodore."

"Oh," Theodore smiled and his counterpart, "Morning, Ellie."

Eleanor asked, "So, did you talk to your brothers?"

"Talked to them about what?" Theodore knew what she was talking about, but just decided to play dumb about it.

Eleanor frowned and told him, "Come on, Theodore. You know what I'm talking about."

Theodore sighed answered, "Not yet. I'm waiting for the right time to tell them."

"It's been three months, Teddy. Why haven't you told them yet?"

Theodore answered, "Same reason you haven't told your sisters."

Theodore pointed to Alvin and Brittany as they kept fighting.

"Nuh-uh!"

"Yeah-huh!"

"Nuh-uh!"

"Yeah-huh!"

"Nuh-uh," Alvin smirked, "Infinity."

Brittany growled and pushed Alvin, "I _hate_ you!"

Alvin was pushed to the ground and dropped his skateboard, which rolled away. Alvin quickly chased after it, "My board!"

As he ran off, Brittany yelled, "Serves you right!"

Eleanor chuckled nervously and blushed, "Oh, right."


	2. Chapter 2

Alvin raced through the hall, desperately trying to get his skateboard. As it kept rolling, someone familiar unknowingly stepped on it, making the board steer off its course and into a trash can! As litter flew all over the place, said person was sitting on the ground with the trash can stuck on their upper body.

Alvin picked up his skateboard and shouted, "Finally!" Alvin then noticed the person in the can, who was now muttering angrily, so Alvin grabbed onto the can and pulled. As the can came off, he said, "Sorry about that, man. I was…" Alvin gasped.

The person who stopped Alvin's skateboard was none other than his next door neighbor, Lawrence Talbot. Mr. Talbot glared at the 14 year old Chipmunk and growled, "Alvin Seville…"

Alvin gulped and shivered, "M-m-m-Mr. Talbot. W-why are you here?"

As Mr. Talbot stood up, he dusted himself clean of litter and explained, "I may have neglected to mention this, but the School Board has moved me to the High School as the new principal. Today's youth needs much guidance, and they say I'm the one for the job." Principal Talbot glared daggers at the red clad Chipmunk and said, "Understand, Mr. Seville, I will not tolerate such incidents. I'll let you go with a warning, but next time, be prepared to face the consequences. Understand?"

Alvin nervously answered, "Yes, sir."

"Good." Principal Talbot shooed away Alvin, "Now, run along. You needn't be late for class."

Alvin picked up his board and walked back to his locker. A moment later, he finally got there and when his younger brother, Simon, noticed the look on his face, he asked, "Alvin, what happened? You look like you saw a ghost."

"Worse. I saw Principal Talbot."

Everyone gasped at the name and Simon asked, "Talbot is the principal?"

Alvin explained, "Long story short, it was the School Board's doing."

Theodore commented, "I don't know. Maybe this is a good thing. Principal Talbot already knows us, so maybe he'll go easy on us."

Alvin scoffed, "Fat chance."

After that, Alvin opened up his locker, and as he tried to put his skateboard in it, it was quickly slammed close by a teen wearing a letterman's jacket. This teen had two other letterman sporting teens and a girl in a cheerleader's outfit with him. The teen was an average build, had neatly cut blonde hair, and wore a black shirt under his jacket, blue jeans, and sneakers. The other two teens wore the same thing, and one was bald with much muscle and the other was black with his hair in dreads. The cheerleader had blonde hair in a ponytail, wore a blue, white, and gold outfit with matching pom-poms, and had on pink lipstick. The blonde teen asked, "And just what do you think you're doing?"

Alvin said, "I was putting my board in my locker."

The blonde teen looked to his group and they all started laughing! The blonde stopped, causing the others to stop, and he said, "Sorry, kid, but _these _lockers belong to us."

Alvin got in the kids face and said, "Who says?"

"Says me, kid! These lockers belong to the Seniors, and that would be," The blonde teen mockingly took a moment to think about and said, "Us!"

Simon lightly pushed Alvin aside and told the teen, "Pardon me, but I'm afraid that you cannot commandeer these lockers. They have been assigned to us by the school, and…"

"Blah, blah, blah, blah! Listen, glasses…"

"My name is Simon."

"Don't care. If you know what's good for you, you'll move along."

Jeanette moved to the Simon and whispered, "Simon, please. Let's just go before something happens."

The blonde cheerleader mockingly said, "You'd better listen to her."

The blonde said, "Yeah, _Simon_. Just go before something happens."

"Like what?"

"Like this." The blonde snapped his fingers and said, "Bull, get the book!"

The bald, muscular one said, "Right, Josh!"

Bull swiped the book Jeanette was holding was swiped away from her and held it far up, so she couldn't reach it. Jeanette gasped, "Give it back!"

The black kid told her, "Okay. We'll give it back if you return those melons you stole."

"What?" Jeanette asked in confusion, "I don't have any melons."

"Sure you do. They're in your shirt!"

Jeanette quickly realized what he meant, and with a blush, quickly covered her chest with her arms.

The group laughed at this joke, and Josh put his arm around the black kid, "Nice one, Lamar!" Josh and Lamar shared a fist bump.

Brittany yelled at Josh, "Hey! You can't pick on my sis like that!"

Eleanor joined his sister and said, "Why don't you pick on someone your own size?"

Josh asked, "Like… you?"

Brittany and Eleanor gulped and Ellie said, "Uh… actually, we're a lot shorter than you."

Alvin tried walking over to Josh, but Theodore gripped his arm tightly, "Alvin, don't! You'll get hurt!"

Alvin quickly pulled his arm away from Theodore and approached the blonde headed bully, "Look here, you jerk! We…"

Without warning, Josh turned around, picked up Alvin by his shirt, which caused Alvin to drop the skateboard, and slammed his against the lockers, "What did you call me?!"

Alvin gulped and chuckled nervously, "A…" Alvin hesitated when he saw the look of pure rage in Josh's eyes, "Jerk?"

Josh growled, and pulled back his fist to punch Alvin, which caused the other teen Chipmunks to gasp in terror, until his arm was stopped by a large, adult hand, "Mr. Masters, I assume?"

The group of 10 teens gasped as they saw, "Principal Talbot?!"

Talbot told Josh, "Mr. Masters, unhand Mr. Seville this instant!"

Josh quickly unhanded Alvin and quickly changed his tone to sound like a total suck up, "Mr. Talbot! I've heard good things, sir! How's your day?"

"Save it!" Talbot barked, causing Josh to shut up, "There's a lot of things I do not tolerate, Mr. Masters, and bullying is one of them. I'll let you off with a warning this time, but if I were you, I would watch my temper around the new students, or else!"

Josh gulped and said, "Yes, sir."

"Good." The bell rang and Talbot told the group, "Now, off to class. All of you!"

As Talbot walked away, Josh told Alvin, "You got lucky this time, _Freshman_." Josh let out a hiss as his said 'Freshman'.

Alvin told himself, "Something tells me this year isn't going to end well."

Brittany mocked, "You think?"

**Not much, I'll admit, but they'll get longer.**


	3. Chapter 3

**Hello, readers! Extremely sorry for not writing for so long. Life and such, but I've finally found some time and inspiration to write again, so here's the next chapter for ya!**

In the class across from the lockers, the group of 7 had taken a seat in 7 desks. The desks were arranged into 5 rows that went from left to right and 6 columns that went up and down. The Chipmunks took a desk in the 2nd row, with Alvin, Simon, and Theodore arranged from left to right. Behind them, in the 3rd row, the Chipettes sat the same, starting with Brittany to the left, Jeanette in the middle, and Eleanor to the right. There were a total of 27 students in the class, leaving a seat in the 3rd row unoccupied, as well as 2 seats in the last row. At the front of the classroom, there was a 30 something year old female, who was wearing a black blouse, a maroon jacket, maroon skirt, matching maroon high heels, and a golden heart locket around her neck. She had jet black hair that feel to her back, blue eyes and a beauty mark on her left cheek. "Good morning, class," the woman told the students with a smile, "My name is Mrs. Florence Blackstone, and I'd like to welcome you all to your first year. Now, as you already know, in Homeroom, this is your time of the morning to do as you wish before your classes, so long as it doesn't involve anything illegal or reckless," Mrs. Blackstone peered at Alvin, "Alvin Seville."

Alvin chuckled nervously and waved, "I guess my reputation perceives me."

"To a T, Alvin," Mrs. Blackstone smiled again and continued, "However, before we get to that, I will read you our daily announcements, as I will every morning. Okay, so…"

While Mrs. Blackstone spoke, a young boy in front of Alvin turned around and asked in a hushed tone, "Hey, aren't you that kid who stood up to Josh in the hall?"

Alvin answered, "Yeah! How'd you know?"

The boy replied, "Me and some other students saw it happen. Pretty gutsy, but stupid."

The boy sitting next to Alvin leaned in and said, "Josh is the Big Man on Campus. It's not wise to get on his bad side."

Mrs. Blackstone called out, "Mr. Seville, Mr. Weisman, Mr. Long. Is there something you'd like to share with the class?"

All three boys answered, "No, Mrs. Blackstone!"

"Good."

As Mrs. Blackstone went back to talking, Simon leaned in to his brother and whispered, "Way to go, Alvin."

After Home Room, the bell rang and the Munks and Ettes gathered around their lockers to finally put up their stuff. Jeanette asked, "So, that bully is the Big Man on Campus?"

Alvin answered, "That's what that kid told me."

Brittany scoffed, "Leave it to Alvin to kill our chances of a good first year."

Alvin instantly snapped, "I didn't ruin anything!"

Brittany snapped back, "You pick a fight with the Big Man on Campus and saying you 'didn't ruin anything'? Is there even a brain in that giant rock you call a head?!"

As the two continued bickering, the other 4 teens did the same thing and stayed out of it.

Simon chuckled and said, "Not to sound a cliché, but those two are crazy for each other. It's too bad they're still in the 'Kindergarten' mode of their feelings."

Eleanor followed up with, "So true. It'd make things easier for us all if they'd just admit their feelings," Ellie looked right at Theo and asked, "What do you think, Theodore?"

Theodore got nervous and said, "I think I gotta use the bathroom!"

As Theodore ran off in the opposite direction of the bathroom, Eleanor said, "Oh, yeah. I'm sure."

Three halls down, Theodore quickly hid in the janitor's closet. He was heavily panting and wiped some sweat from his brow, "Phew!"

The door quickly swung open and Eleanor said, "Theodore…"

Theodore came out of the closet and sheepishly smiled. Eleanor simply frowned angrily, causing Theodore to frown sadly. Eleanor sighed and said, "Theodore, I know it's not going to be easy, but at some point, we have to tell the others we're…"

"I know, I know," Theodore cut her off, "But the problem isn't all of them. Jeanette and Simon won't have a problem with it, but Alvin and Brittany…"

"I know, Theodore. Those two can be... difficult, but when we find the right time, I'm sure they'll accept it."

Theodore sighed, "I guess you're right."

Just then, the bell rang and Eleanor said, "Well, we'd better get to class."

"Yeah."

**Sorry for the short chapter! My chapters will probably vary from short to long, but it is what it is. Hope you liked it!**


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